IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Intelligent article to control the internal pressure in continue in bottles

An intelligent packaging might, among others, provide information and allow monitoring of the quality of the packed product or its surrounding environment. A recent project on micro-flow wine bottles closed with aluminium screw cap and tightness liner, highlighted the importance of monitoring the internal overpressure continuously, in real-time and at least for 72 hours, since the internal pressure on the tightness liner and the micro-flow are related. Real-time and continuous measurements are not the standard methods of measurement of the overpressure, yet. The most used equipment for the determination of the pressure in wine bottle is the aphrometer, a destructive device that supplies a single value of pressure.

Design of microbial consortia to improve the production of aromatic amino acid derived compounds during wine fermentation

Wine contains secondary metabolites derived from aromatic amino acids (AADC), which can determine quality, stability and bioactivity. Several yeast species, as well as some lactic acid bacteria (LAB), can contribute in the production of these aromatic compounds. Winemaking should be studied as a series of microbial interactions, that work as an interconnected network, and can determine the metabolic and analytical profiles of wine. The aim of this work was to select microorganisms (yeast and LAB) based on their potential to produce AADC compounds, such as tyrosol and hydroxytyrosol, and design a microbial consortium that could increase the production of these AADC compounds in wines.

Prevention of wine oxidation during barrel aging: an innovative method to measure antioxidant

Wine oxidation is a problem that affects the freshness, the aromatic profile, the colour and also the mouthfeel of the wine. It mainly concerns white wines. Oxygen interactions with wine compounds lead to the phenomena cited above that are responsible for the depreciation of these wines. Barrel aging is a crucial step in the wine process because it allows many modifications as wine enrichment, colour stabilization, clarification and also a slow oxygenation of the wine. Effects of the oak barrel have to be known to prevent oxidation of the wine. We have been interested in the main antioxidant compounds released by oak barrels to the wine and we have developed an innovative method to reach directly these antioxidant compounds at the oak stave surface.

Application of UV-B radiation in pre- and postharvest as an innovative and sustainable cultural practice to improve grape phenolic composition

Ultraviolet radiation (UVR) is a minor part of the solar spectrum, but it represents an important ecological factor that influences many biological processes related to plant growth and development. In recent years, the application of UVR in agriculture and food production is emerging as a clean and environmentally friendly technology.
In grapevine, many studies have been conducted on the effects of ambient levels of UVR, but there are few considering the effects of UV-B application on grape phenolic composition under commercial growing or postharvest conditions.

Highlighting the several chemical situations of Dimethyl sulfide in wine

Dimethyl sulfide (DMS) is a compound that accumulate in wine for the early years of ageing 1. During this stage, which is often carried out in the bottle, the environmental conditions are conducive to the release of DMS from its precursors, already present in grapes2